Water → HCID 89666839, compound

HRID 2171227Notes

Reaction equation

HRID 2171227 reaction equation
O.O.[OH-].[Li+].[F:5][CH:6]([F:25])[O:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[N:10](C(OCC)=O)[N:9]=1>C1COCC1>[F:25][CH:6]([F:5])[O:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[NH:10][N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89666801HCID 89666801, compound

Product 1

HCID 89666839HCID 89666839, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Water (6 ml) and lithium hydroxide monohydrate (640 mg) were added to a THF (19 ml) solution containing ethyl 3-(difluoromethoxy)-5-nitro-1H-indazol-1-carboxylate (1.14 g) obtained in the 1st step, followed by reflux at 80° C. for 3 hours. THF was distilled away under reduced pressure and a saturated ammonium chloride aqueous solution was added. An insoluble precipitate was removed by filtration. The obtained residue was washed with water, dissolved in ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. A yellow solid of 3-(difluoromethoxy)-5-nitro-1H-indazole (921 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. distillationTHF was distilled away under reduced pressure
  3. additiona saturated ammonium chloride aqueous solution was added
  4. customAn insoluble precipitate was removed by filtration
  5. washThe obtained residue was washed with water
  6. dissolutiondissolved in ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-476f48a6bfda4d9fbd4f5497fe4a4604
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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